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Conversation with Heather Dugan on Relationships, Life, and Ruth Bader Ginsburg: Author


Author(s): Scott Douglas Jacobsen

Publication (Outlet/Website): In-Sight: Independent Interview-Based Journal

Publication Date (yyyy/mm/dd): 2020/10/08


Heather Dugan is an author, advice columnist, and feature writer. She was a finalist in the USA Book Awards and the Indie Next Generation Book Awards. She recently published Date Like a Grownup. She discusses: dating like a grown up; look to someone as a potential partner or someone as a summer fling; change and growth; lifestyle and potential preconditions; the narrative inside of the woman’s mind; young woman vet ‘sharks’ or inauthentic men; the challenge for Millennial women looking for relationships; factors are the most important to make a relationship last; the loss of the late Ruth Bader Ginsburg; persistence; women to see themselves as making independent choices in more connection with their real selves in their lives; and challenges rather than primarily as tragedies.

Keywords: Heather Dugan, life, love, relationships, Ruth Bader Ginsburg.

Conversation with Heather Dugan on Relationships, Life, and Ruth Bader Ginsburg: Author

*Please see the footnotes, bibliography, and citation style listing after the interview.*

Scott Douglas Jacobsen: When you’re considering dating, and dating like a grown up, what are some lessons you’ve learned in reflection?

Heather Dugan[1],[2]: One of the things that got me started on writing that book. If you had a difficult situation, a lot of friends would like to bail you out, “You can pretend you have an emergency.” I wanted to do it differently. You feel a lot more empowered and happy with your choices if you can face people directly. I started this for Date Like a Grownup: Anecdotes, Admissions of Guilt & Advice Between Friends.[3] The big scenes I come back to are understanding who you are. A lot of the time, people begin dating the second time around thinking that they’re the same person as the first time around. They don’t realize, maybe, that they’ll be looking for different qualities.

Have yourself in a position where you have a life bigger than dating, it means that you need good, strong friend relationships. [Laughing] Otherwise, it is like trying to find dinner in a convenience store when starving or hungry.

Jacobsen: [Laughing].

Dugan: Then you tend to grab the least-worst option or the last text message. If you’re solid in your self-understanding, then you can wait for the best fit for you. It fits into some other things like filtering out people who may be nice, but do not fit. It is a self-assessment – being honest with who you are. We have such need for a relationship. Where they will cloak a candidate with all of their hopes and dreams, they want to see this persona s the person that they want. Something that resembles a dream. Then the person [Laughing] does a bad little strip tease and reveals who they are. You just weren’t will to see that.

Jacobsen: This is good information. Also, the framework for coming to vet a potential candidate – let’s call them – for a relationship, this will differ for each individual, but there are trends in terms of what people want where they are in life. For someone of a younger cohort, how do they, typically, if they are a young woman, look to someone as a potential partner or someone as a summer fling – so to speak?

Dugan: My book is really geared more towards for people looking for the long-term relationship. I don’t think that you need to filter. If that is your intention, short fling, there are some things. It is where your attraction is; that is what that boils down to. You may want some shared activities. If you want some legs on it, you have to look deeper than that. Because you can find chemistry in shared activities a lot of different places. If you want it to last longer than a summer, you have to find some other commonalities. One of the big things that will make the difference is static versus a dynamic partner.

It can cause a lot of friction. One wants to stay the same. They aren’t curious. There is nothing wrong with that. But that kind of person is not going to be comfortable in being with someone who wants to learn and grow. Even two people who want to grow, they may not even have the exact same interests. I think it is important to have the same mindset of the curiosity. Because you will always have things to share. Actually, it is better if you don’t share your whole lives together. Otherwise, you suck the oxygen out of the relationship.

Jacobsen: When we talk about change and growth, change is more neutral and can go in any number of directions, including dissolution. Growth has more positive connotations. It has this sense of adding things to the unit, to the couple, rather than detracting from it. What are the positive things, concrete manifestations, of growth here?

Dugan: A lot of times, this last book I wrote about the transitions of people individually, but the effects on couples as well. These are life changing events. When a couple weathers things together, they find strength and learn to appreciate and rely on each other in new ways. Other times, the deficits become clear. If a couple is to grow, then I think it is a matter of each of them being able to use the strengths of them. It takes knowing the strengths of the other person and the strength of oneself. Growing, it is creativity in there too. If we are growing, we are trying new things. One of my lessons to my youngest, “You saw the mistakes of your sister. You saw the mistakes of your brother. Make your own mistakes.”

Obviously, with a couple, in the context of a romantic relationship, you want to be growing, learning. A manifestation – to be more specific – is growing together and finding new things to talk about, new activities to share together, probably meeting new people to talk with. A lot of it is fresh water flowing into the relationship. It guarantees that you’re going to have new information, new opportunities. It is what tends to drive the growth. It is integrating what you’re learning into your life.

Jacobsen: For young women, younger people in general, they, typically, do not have to worry about a lot of health issues. As they get older, the probability of them having any variety of health issues from the very severe to the minor rise. Different health issues arise as well. When people are looking for the long-term partner when they are younger, how should they factor into account lifestyle and potential preconditions an individual might have who they might be looking to have legal and economic ties to – for a lifetime, potentially?

Dugan: In the beginning, if you are young and starting out, philosophy will be important. You mention later having some evidence of those ideas. Are you financially frugal? Do you enjoy spending lavishly? You want to be compatible on that. Part of that is going to be a shared activity thing. Is this somebody who likes to go running or going out, or staying in watching Netflix? Hopefully, your diets are compatible. In terms of health, it is all a roll of the die on it. If you are healthy, hopefully, you will be attracted to someone compatible that way. In the years that transpire, there are other things that grow beyond the initial physical attraction and other things. So, you’re able to weather things like a health issue.

Because, big and small, they do happen. People do bump into things. You do get stronger. I’ve had ankle surgery. I am still hiking in Colorado. You learn to push through. If you are in a couple, it becomes part of your story. Anytime you can make something part of the story. It is good.

Jacobsen: When a relationship is going well for an older person, what is the narrative inside of the woman’s mind? If a younger woman, what is the narrative there as well? Are there differences, in other words?

Dugan: I will have to think about the younger side of it. Because people share things, but you don’t know the whole internal narrative. You always begin relationships with a lot of hope and with a lot of history. Older people have more history. A lot of times, I think that can put a ballast on it. But it doesn’t make it go away. People react in different ways. It depends on how mentally healthy they are. Some people, unfortunately, have a difficult time without drama. I do a lot of speaking on relationships in general. It is so important to catch. People do these patterns based on past experiences, which end up sabotaging relationships, sometimes.

If things are going well, and if the person is emotionally healthy, then the excitement comes from enjoying life together rather than creating drama. There is some peace in that. But you are planning for a future they share. Again, for the younger, there is not the history there. But everyone brings some history. In the beginning, you are dating the possibility of a person, almost. As we go along through life, we get chiselled. It is almost like a sculpting process. I see that happening. You reveal more and more of yourself as you grow into yourself.

Jacobsen: How can a young woman vet ‘sharks’ or inauthentic men who can make wild promises but have no intention of fulfilling them? Or are simply not competent in life, in life tasks and goals, to fulfill some of the promises that they make, even with good intent?

Dugan: It is important to give people time to show who they are. It is difficult to know, immediately. You may have clicks on things that look like a relationship will go a while. But you have to have some glitches along the ay. You have to deal with a malfunctioning toilet or delaying travel plans. Travelling together is a great way to see how flexible people are; somebody might make promises. You look for how they treat you. Words are one thing. What do they do? I often tell people in terms of evaluating the quality of the relationship.

A lot of people, they are weighing it, “Is it valuable to say or should I move on?” Is it diminishing you? Are you able to be your best self? If anybody is having to diminish who they are in order to keep the relationship afloat, it is not going to work in the long-term. That’s a time to have, at least, a discussion together to see if it is something that can be understood and rectified. But that situation, if somebody is squashing somebody else’s capacity to grow or is trying to keep them within a certain framework, then you’re likely to get to get a defensive response. It is better to live alone than to not live authentically as yourself.

Jacobsen: What do you see as the challenge for Millennial women looking for relationships, family, if they are heterosexual, a husband and family? As Pew Research finds, most young men and women do want marriage and family in the United States.

Dugan: I’ve encouraged my children. I’ve told them, “Don’t get married until you’re at least 30.” It is great if you can find someone who you click with and can do things together. There is no rush. You need to be stable in who you are before having children. It launches you into another orbit. I’ll be honest. It is not like you become a parent and suddenly have everything figured out. It is one of the first things I had my kids understood when they were older. “You’ve got it from here.” We don’t have to start a family immediately. I can understand when some people are tentative to move in that direction. I hear what you’re saying, ultimately. It is important to make sure it is a solid relationship. There are a lot of wobbly things in the world right now.

Hopefully, a relationship when you’re younger makes things in the world a little more stable, at least in your vicinity. Is it easy to relax with them? I remember back in relationships. Here is one party that is happy, which has nothing to do with me, it is something carried with them. People show you their best self. That is what we do. Over time, more and more, we reveal parts of ourselves that we are unsure of being worthy for other people to see.

Jacobsen: What factors are the most important to make a relationship last? Based on the research and the advice in the column, what strategies should people keep in mind?

Dugan: I think flexibility is huge. Rigidity has killed more things. It is difficult when people decide there is one way of living, one way of doing things. It is important to embrace things that come your way, to incorporate that into what you’re already building. Kindness, you have to be able, even in the midst of difficult times when there is a crisis or someone is not feeling well/afraid, to know the line and not to vent on your partner. To be kind, it is final. That’s what keeps things afloat, I think. Showing respect, you will not agree on everything. Respecting their choices and letting them have them, that shows love to the highest.

Unfortunately, it is hard to dial it down to a couple. But flexibility, kindness, respect, and a sense of commitment to something bigger than yourself, the promoting of each other in terms of appreciating their ability to be their unique self, not wishing for some other self – letting them be their self on their time. So, you can have the safe, calm space or a haven from the world.

Jacobsen: Unfortunately, there was the loss of the late Ruth Bader Ginsburg late last month. She has been a pillar for a lot of women’s rights progress, nationally, in the United States, whether in Supreme Court decisions or in commentary. So, as a mother, how can you approach speaking about the legacy of former Justice Ginsburg in regards to the work that she has done, and the strength of women and the importance of gender equality in the United States?

Dugan: I like to use those conversations as a way of empowering my kids and to help them tap into their own possibilities. On the topic of legacy, I would begin talking about how these develop over time. She didn’t become a circuit judge until 60. There’s a lot of work there. A lot of constancy, integrity, to get to the position, to be the same in all situations. The reliability of the decision-making there for her. It is helping your daughter understand who RBG is to so many people and thinking, maybe, the things she would hope people know about herself. Now, and what kinds of things would she like to build towards for her own legacy, another thing, too, the consistency thing; the constancy of being the same person in all situations. It is important to talk about integrity and to be the same in all situations.

It can be difficult for young women and for young men for that matter. Can you be the same person with your friends group? It is understandable that, maybe, you speak differently with adults than with kids. Are you able to be the same person with adults and with kids? If you are a person of respectful of other people’s ideas, are you different with one friend group than with another?

Jacobsen: You had a note about persistence as well. What is the example of persistence in Ginsburg’s life?

Dugan: The whole going first thing, my kids have heard a lot, “If not you, then who?” The idea that somebody has to take the first step for things to change. It wasn’t one step. As we said, her legacy, she went at this creatively. She was striving for equality through the use of the law, but she came at it through different viewpoints. As part of her push for women’s rights, she argued widowers should receive death benefits. It was creative to find that and make that as part of the puzzle. I would go on to the value of creative problem solving, where there are different approaches for the same situation to move yourself forward. Talking about what it means to be a pioneer, that “no” is always part of the process. You are going to hear, “No.” Women need to understand it. Because they are going to hear it. When I was younger, “No,” would stop me in my tracks, now, it is more information.

Jacobsen: [Laughing].

Dugan: It is not judgment on a person. When they are more aware, then they can blow through them easier and then make their next attempts, I would ask about times when she heard, “No,” when she thought that she should have heard, “Yes,” when she thought that she was capable. Arming our kids with those first words, so they have that launching pad, the moment when you are first feeling the stress of the situation. It can be hard to find the words. It can give them the confidence to push past and find the dialogue rather than giving up. RBG, her life is such a rich history and example. There are a lot of different answers to learn on how she progressed through her journey.

Jacobsen: How can one allow women to see themselves as making independent choices in more connection with their real selves in their lives?

Dugan: I think you have to build that confidence in self. A lot of people spend their 30s, 40s, and 50s repairing a confidence damaged in childhood, unfortunately. Talking with your daughter that she will make decisions totally different from you, it’s totally fine. RBG pursued a different path than her mom. She couldn’t attend college. But her mother was her fan. Talk about the ways the two of you are similar and different, it allows her to be different within the family. The fact that she can change her mind. That’s part of gaining information. It does mean that you do change your mind. RBG exhibited an open-mindedness, even as she held onto core values. She socialized quite a lot with Scalia. There are a lot of great anecdotes out of that. Her challenges made her stronger, because of him. If you integrate the good parts into your own, and crystallize what you really good think, it is a good thing. We need discuss active listening and discussing vs. arguing, being able to take in the information the other person is preparing rather than preparing the rebuttal [Laughing].

Jacobsen: [Laughing].

Dugan: It is affirming that that is a sign of strength. That apologizing is a sign of strength. She apologized for comments about Donald Trump and Colin Kaepernick. She said things that she thought later weren’t the best and was strong enough later to say that. Saying, “Sorry,” doesn’t make you a weaker person, it makes people respect you more if you own up to it. Was there a time when people apologized to you, and then you liked them better because you felt they were more real with you? Maybe, you ask about times that she’s gotten information and changed her own mind. It will help her be more open to that kind of thing.

Jacobsen: As a wrap-up question for the session today, I want to ask about some of your difficulties in your life that you have experienced and taken those on board as challenges rather than primarily as tragedies, so as to become stronger.

Dugan: It has been a journey [Laughing]. Now and then, people will say, “You’ve had such a charmed life.” I just want to laugh [Laughing]. I had a call today. I mentioned. There was a time in life when I lost three close family members, had a major surgery, was going through divorce proceedings, was trying to raise kids as a single mother, and my mother required care. I got very disconnected from the whole world. It was a very difficult, dark time. I didn’t know that I could create anything better out of my life. I think my children were part of it, certainly, of moving forward. It was a greater responsibility for everybody. If you have something bigger than yourself, then that always helps. I have always been one of those people who has been curious. There is always an expectation. I want to see what it is [Laughing].

I’ve mentioned the previous ankle surgery. I find workarounds. Most of the time, when something is blocked, I have begun to find ways around them and see them as detours. Plan B is almost always better than Plan A because it includes possibilities and spontaneity, which didn’t enter my brain. I didn’t have the idea. [Laughing] I think having this sense of purpose and looking for workarounds in Plan B. It makes all the difference. The purpose part, for me, is helping other people maximize their life experience. It is such a big and important purpose. I don’t think I could stop.

Jacobsen: Heather, it’s been a delight. Thank you so much for your time today.

Dugan: Well, thank you, I appreciate chatting. If I can ever help you with anything, just give me a call.

Appendix I: Footnotes

[1] Author; Columnist.

[2] Individual Publication Date: October 8, 2020:; Full Issue Publication Date: January 1, 2021:

[3]Blurb from Amazon (Hyperlinked in the main text): “Date Like a Grownup examines the impact of loneliness and social obsolescence on men and women in their second single lives and provides punctuating proof that looking for love from a place of isolation is as unwise as grocery shopping on an empty stomach. A USA Book Awards and Next Generation Book Awards finalist, Date Like a Grownup is “a witty and insightful look at dating the second time around, “a refreshing peek into the challenges of building midlife relationships” and “a toolkit for moving past the loneliness toward a relationship built for the future.” Unlike most relationship manuals, this book does NOT guide the reader through game-playing and winning temporary partners. Instead, Ms. Dugan presents a personalized strategy for building a life foundation that facilitates finding and growing a “right fit” relationship. Topics include: effective filtering, social media and online dating, how to avoid isolation and “space-filler” choices and how to strategically begin building a larger social network. Engaging narratives such as “The Percocet Proposal” and “Need Meets Greed” underline specific dating principles outlined in the book and affirm that none of us are immune to bad choices. These real-life outtakes from interviewed men and women are often funny and always insightful. Heather Dugan is a speaker, discussion facilitator and connection coach, a writer/advice columnist and frequent media expert on topics related to relationships, dating, connection, combatting isolation and work/family issues. Founder of Cabernet Coaches, a social connection group that encourages and enables women to build bigger relational foundations, Heather is dedicated to high impact, face-to-face friendship as a means of change. Her videos, articles and books promote active enablement, meaningful connection and proactive decision-making with a twist of humor and the affirming good nature of a friend who has traveled the same road. With at least half of adult population attempting a Do-Over on their most committed relationship—and many getting it wrong yet a second time—Date Like a Grownup provides time-saving truths for the millions of men and women navigating midlife dating.”


In-Sight Publishing by Scott Douglas Jacobsen is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License. Based on a work at


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